Carbon Dioxide → HCID 66758895, compound

HRID 1635538Notes

Reaction equation

HRID 1635538 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[CH:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[CH2:7][C:6]=2[CH:32]=1.CCCCCC.C([Li])CCC.[C:44](=[O:46])=[O:45]>C1COCC1>[C:44]([C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[CH:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)[CH2:7][C:6]=2[CH:32]=1)([OH:46])=[O:45]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 66758102HCID 66758102, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 66758895HCID 66758895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[3-(8-Bromo-5,11-dihydro[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]-4-(4-chlorophenyl)piperidine (Example 160) (130 mg) in THF (1.0 ml) was added 1.6M n-butyllithium hexane solution (0.17 ml) at −78° C. After stirring 10 minutes at the same temperature, CO2 (dry-ice) was added to the mixture. After being warmed to ambient temperature, the mixture was stirred for 30 minutes at the same temperature. The mixture was concentrated in vacuo. The resulting oil was purified by silica gel chromatography eluted with dichloromethane -methanol (5:1) to give the titled compound.

Workup

  1. additionwas added to the mixture
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe resulting oil was purified by silica gel chromatography
  4. washeluted with dichloromethane -methanol (5:1)

Sources & evidence

ORD record
ord-8787ba9f1e79409ba0d207dd70dd6417
Source dataset
uspto-grants-2003_01
Patent number
US06509346B2

Reaction notes

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